1-Hexyne → HCID 86592816, compound

Participants

Reaction Steps

2-(1-hexynyl)adenosine (Compound 3).8 The reaction was performed with 2-iodoadenosine (1, 255 mg, 0.65 mmol) and 1-hexyn (3.15 mmol). The mixture was purified by column chromatography (5% MeOH in CH2Cl2). Yield 192 mg (0.55 mmol, 85%), mp 106–109÷C; Rƒ 0.10 (10% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 8.37 (s, 1H, H-8), 7.41 (bs, 2H, NH2), 5.84 (d, J=6.18 Hz, 1H, H-1′), 5.45 (d, J=6.18 Hz, 1H, OH-2′), 5.22–5.16 (m, 1H, OH-5′), 5.22–5.16 (m, 1H, OH-3′), 4.52 (q, J=5.15 Hz, 1H, H-2′), 4.11 (q, J=3.43 Hz, 1H, H-3′), 3.93 (pd, J=3.43 Hz, 1H, H4′), 3.65–3.48 (m, 2H, H-5′), 2.39 (t, J=6.86 Hz, 2H, ≡CCH2), 1.51–1.39 (m, 4H, CH2CH2), 0.90 (t, J=6.87 Hz, 3H, CH3); MS m/z 348 (M+H)+; Anal. (C16H21N5O4 0.22 CH2Cl2) C, H, N.

Provenance & Evidence